EP0363730B1 - Colorant monoazoique de couleur stable, sa préparation et son utilisation - Google Patents

Colorant monoazoique de couleur stable, sa préparation et son utilisation Download PDF

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Publication number
EP0363730B1
EP0363730B1 EP89117830A EP89117830A EP0363730B1 EP 0363730 B1 EP0363730 B1 EP 0363730B1 EP 89117830 A EP89117830 A EP 89117830A EP 89117830 A EP89117830 A EP 89117830A EP 0363730 B1 EP0363730 B1 EP 0363730B1
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EP
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Prior art keywords
modification
dye
dyeing conditions
heated
under dyeing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP89117830A
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German (de)
English (en)
Other versions
EP0363730A3 (fr
EP0363730A2 (fr
Inventor
Hubert Kruse
Konrad Dr. Opitz
Ulrich Dr. Bühler
Willi Dr. Steckelberg
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis Deutschland GmbH
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella AG
Cassella Farbwerke Mainkur AG
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Application filed by Cassella AG, Cassella Farbwerke Mainkur AG filed Critical Cassella AG
Publication of EP0363730A2 publication Critical patent/EP0363730A2/fr
Publication of EP0363730A3 publication Critical patent/EP0363730A3/fr
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Publication of EP0363730B1 publication Critical patent/EP0363730B1/fr
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
    • C09B67/0015—Influencing the physical properties by treatment with a liquid, e.g. solvents of azoic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0025—Crystal modifications; Special X-ray patterns
    • C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
    • C09B67/0029—Crystal modifications; Special X-ray patterns of azo compounds of monoazo compounds

Definitions

  • the present invention relates to a new color-stable crystallographic modification (" ⁇ -modification") of the dye of the formula I. with the X-ray diffraction diagram (Cu-K ⁇ radiation) with the following lines at a diffraction angle of 2 ⁇ (°): Lines of intense intensity: 4.8; 25.4; 26.2; Medium intensity lines: 7.6; 8.1; 14.5; 19.7; 20.5; 21.5; 22.9; 23.8; 24.3 Low intensity lines: 6.2; 6.6; 11.1; 11.8; 12.4; 13.0; 13.6; 15.3; 18.7; 28.0; 28.7; 29.4; 30.5; 31.5; 32.3.
  • the X-ray diffraction diagram of the color-stable ⁇ modification recorded with Cu K ⁇ radiation is shown in FIG. 1.
  • a computer-controlled Siemens D 500 powder diffractometer was used to record the X-ray diffraction patterns.
  • the dye of the above formula is aqueous by diazotizing 2,4-dinitro-6-chloro-aniline in concentrated sulfuric acid and then coupling the diazo solution thus obtained with 4-propionylamino-2-N-ethylamino- (2-methoxy) ethoxybenzene receive mineral acid medium.
  • the color-unstable ⁇ modification is shown in the X-ray diffraction diagram (Cu K ⁇ radiation) shown in FIG. 2 with the following lines at a diffraction angle of 2 ⁇ (°): Lines of intense intensity: 5.2; 7.5; 11.9; 23.2; 24.5; 25.5; 27.2; Medium intensity lines: 5.9; 9.5; 10.8; 15.9; 19.4; 20.5; 21.3; 22.5; 23.9; 26.5; 28.6; 29.2; 31.3; 31.9; 33.2; Low intensity lines: 13.4; 15.2; 16.5.
  • the dye-unstable ⁇ -modification of the dye of the formula I is converted into the dye-stable ⁇ -modification by heating to temperatures from 60 to 180 ° C., preferably 80 to 140 ° C.
  • This heating can be carried out in various ways.
  • the dye-unstable ⁇ -modification is heated to the temperatures mentioned, preferably with stirring, in aqueous suspension. It is advisable to adjust the pH of the aqueous suspension to approximately neutral. If necessary, surface-active compounds and / or solvents are added to the suspension to be heated. When heating to temperatures above the boiling point of the liquid phase, the application of positive pressure is required.
  • the heating is carried out until the ⁇ -modification has been converted into the ⁇ -modification, which usually takes 2 to 6 hours. The conversion can be followed by X-ray analysis or microscopy on samples taken.
  • Surface-active compounds can be anionic, cationic or nonionic and, for example, dispersants, Represent emulsifiers or wetting agents.
  • Suitable surface-active compounds are, for example, sodium diisobutylnaphthalenesulfonate, adducts of ethylene oxide and / or propylene oxide with fatty alcohols, such as, for example, the adduct of 25 mol of ethylene oxide with 1 mol of stearyl alcohol or with 2 mol of ethylene oxide with 1 mol of lauryl alcohol, mixtures of alkyldimethylbenzylammonium chlorides, phosphoric acid ester polychloric acid, fatty acid ester polychloric acid, fatty acid polyalcoholal ester, fatty acid polyalcoholal ester, fatty acid polyalcoholal ester, fatty acid polyalcoholal ester, fatty acid ester polychloric acid, fatty acid ester polychloric acid, fatty acid ester polych
  • Surfactants can be used individually or in combination. 1 to 500% by weight, preferably 5 to 400% by weight, of surface-active agents, based on the ⁇ -modification to be converted, are normally used.
  • solvents are added to the aqueous suspension, those which are water-soluble, such as e.g. Methanol, ethanol, isopropanol and isobutanol.
  • the heating can also be carried out in the course of the customary conversion of the dye into a high fine distribution (finish).
  • the dye-unstable ⁇ -modification is carried out, preferably with the addition of dispersants, such as polyvinyl sulfonates, condensation products of naphthalenesulfonic acid and formaldehyde or of phenol, formaldehyde and sodium bisulfite, alkali salts of lignin sulfonates or sulfite cellulose waste liquor, and, if appropriate, other customary additives (such as, for example, dust protection, antifreeze , Wetting agents, dehydration inhibitors etc.) wet on conventional devices, such as mills or kneaders, converted into a finely dispersed form.
  • dispersants such as polyvinyl sulfonates, condensation products of naphthalenesulfonic acid and formaldehyde or of phenol, formaldehyde and sodium bisulfite,
  • Suitable mills are, for example, ball, vibrating, pearl or Sand mills. If the conversion of the dye into a finely dispersed form is carried out at the temperatures mentioned from 60 to 180 ° C., preferably 80 to 140 ° C., the dye-unstable ⁇ modification of the dye of the formula I is also converted into the dye-stable ⁇ - Modification of the dye of the formula I. If the dye-unstable ⁇ modification is converted into the dye-stable ⁇ modification as part of a fine distribution, temperatures of from 60 to 95 ° C. are normally maintained.
  • the dye-stable ⁇ -modification of the dye of the formula I has not been produced by heating in the course of the conversion into a high fine distribution and is therefore already present in a high fine distribution, it is used for dyeing purposes or for the production of dyeing preparations in the aforementioned in a known manner converted into a high fine distribution.
  • conventional additives such as e.g. Dust protection, frost protection, wetting agents, dehydration preventers, flow improvers etc. added.
  • the dye particles are mechanically crushed until an optimal specific surface is achieved and the sedimentation of the dye particles in a liquid dye preparation or in the dye bath is as low as possible.
  • the size of the dye particles is generally about 0.1 to 10 ⁇ m after the fine distribution has ended.
  • the drying process required for the production of dye powders is carried out in commercially available spray driers.
  • the dye powders can be produced by spray drying the finely divided dye particles present in a ⁇ -modification with a higher thermal load on the dispersion without this being damaged. This increases the space-time yield by increasing the ⁇ T value between the inlet and outlet temperatures of the dryer air.
  • liquid or powdery preparations of the dye-stable ⁇ -modification are suitable without restriction for dyeing fiber materials made from cellulose esters, synthetic linear polyesters, such as polyethylene glycol terephthalate, or blended fabrics of such polyesters with wool or wool at temperatures between 90 and 210 ° C.
  • the preparations which contain the color-stable ⁇ -modification do not flocculate in an aqueous medium and when exposed to high temperatures, which is particularly important for the coloring of packages, for example cross-wound bobbins.
  • the Praxi test allows the suitability of disperse dye preparations for dyeing wound packages to be tested in practice with little effort.
  • a) 100 parts of the dye of the formula I are obtained by diazotizing 2,4-dinitro-6-chloro-aniline in concentrated sulfuric acid and by coupling the diazo solution thus obtained with a weakly acidic solution of 4-propionylamino-2-N-ethylamino (2-methoxy) ethoxybenzene.
  • the coupler used can e.g. Synthesize by ethylation of 2-amino-4-propionylamino- (2-methoxy) ethoxybenzene with diethyl sulfate or by reductive monoethylation of 2-amino-4-propionylamino- (2-methoxy) ethoxybenzene with acetaldehyde.
  • the dye ( ⁇ -modification) is isolated as a water-moist press cake by filtration followed by neutral washing.
  • the dye prepared according to b) is finely divided with 110 parts of a sodium lignin sulfonate, 7 parts of an oxyalkylated novolak and water in a sand mill with cooling (particle size up to 90% equal to or less than 1 ⁇ m) and in an atomizing dryer at an air inlet temperature of 155 ° C and an initial temperature of 80 ° C dried.
  • a powder-free, speck-free setting of the dye is obtained which meets all the application requirements.
  • Example 1 c If the dye prepared according to a) is used in Example 1 c), a powder is obtained under the drying conditions listed, which leads to very spotty block colorations.
  • the dye prepared according to Example 1b) ( ⁇ modification) is ground in a sand mill with cooling using 50 parts of a sodium lignin sulfonate, 25 parts of a condensation product of naphthalenesulfonic acid and formaldehyde and water.
  • the 27% liquid setting obtained is stable in storage, is characterized by level and rub-fast wrap colorations and excellent liquor stability.
  • the dye ( ⁇ -modification) prepared according to Example 1a) is made into a paste with 110 parts of a sodium lignin sulfonate, 7 parts of an oxyalkylated novolak and water, neutralized and stirred at 90-95 ° C. until complete conversion into the color-stable ⁇ -modification (2 to 4 h). After cooling, the suspension is processed into a dye powder as indicated in Example 1c). A powdery setting is obtained which meets all the application requirements.
  • the dye ( ⁇ -modification) prepared according to Example 1a) is heated in an aqueous suspension containing 10% isobutyl alcohol to 90-95 ° C. for 2 hours and filtered off after cooling.
  • the water-moist filter cake ( ⁇ modification) is combined with 110 parts Na lignin sulfonate, 7 parts of an oxyalkylated novolak and water according to Example 1c), finely divided and spray-dried.
  • a powder-free, speck-free setting of the dye is obtained which meets all the application requirements.
  • the dye prepared according to Example 1a) ( ⁇ -modification) is mixed with 110 parts of a sodium lignin sulfonate, 7 parts of an oxyalkylated novolak and water in a sand mill at 80-85 ° C. until fine distribution (particle size up to 90% equal or less than 1 ⁇ m) ground.
  • the color-unstable ⁇ -modification is converted into the color-stable ⁇ -modification.
  • the preparation is dried in an atomizing dryer as in Example 1c).
  • the powdery setting obtained is free of specks and meets all application requirements.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)

Claims (7)

  1. Forme β, de couleur stable du colorant de formule I
    Figure imgb0006
     dont le diagramme de diffraction des rayons X (radiation kα du Cu) présente les raies suivantes pour les angles de diffraction 2ϑ (°) : Raies de forte intensité : 4,8; 25,4; 26,2; Raies d'intensité moyenne : 7,6; 8,1; 14,5; 19,7; 20,5; 21,5; 22,9; 23,8; 24,3 ; Raies de faible intensité : 6,2; 6,6; 11,1; 11,8; 12,4; 13,0; 13,6; 15,3; 18,7; 28,0; 28,7; 29,4; 30,5; 31,5; 32,3.
  2. Procédé pour préparer la forme β de couleur stable selon la revendication 1, du colorant de formule I, caractérisé en ce qu'on chauffe, à des températures de 60 à 180 °C, la forme α de couleur instable, du colorant de formule I.
  3. Procédé selon la revendication 2, caractérisé en ce qu'on chauffe à des températures de 80 à 140 °C la forme α de couleur instable.
  4. Procédé selon les revendications 2 et/ou 3, caractérisé en ce qu'on chauffe la forme α, de couleur instable, en suspension aqueuse.
  5. Procédé selon l'une ou plusieurs des revendications 2 à 4, caractérisé en ce qu'on chauffe la forme α, de couleur instable , en présence d'un ou plusieurs agents tensioactifs et/ou d'un ou plusieurs solvants.
  6. Procédé selon l'une ou plusieurs des revendications 2 à 5, caractérisé en ce qu'on chauffe la forme α, de couleur instable, au cours de la conversion en une forme très finement divisée.
  7. Utilisation de la forme de couleur stable (forme β) du colorant de formule I donnée dans la revendication 1 pour teindre et imprimer des matériaux fibreux à base d'esters de cellulose ou de polyesters linéaires synthétiques ou de tissus constitués d'un mélange de ces matériaux à base de fibres de polyesters et de laine ou de fibranne.
EP89117830A 1988-10-11 1989-09-27 Colorant monoazoique de couleur stable, sa préparation et son utilisation Expired - Lifetime EP0363730B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3834530A DE3834530A1 (de) 1988-10-11 1988-10-11 Faerbestabiler monoazofarbstoff, dessen herstellung und verwendung
DE3834530 1988-10-11

Publications (3)

Publication Number Publication Date
EP0363730A2 EP0363730A2 (fr) 1990-04-18
EP0363730A3 EP0363730A3 (fr) 1991-10-02
EP0363730B1 true EP0363730B1 (fr) 1994-08-31

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EP89117830A Expired - Lifetime EP0363730B1 (fr) 1988-10-11 1989-09-27 Colorant monoazoique de couleur stable, sa préparation et son utilisation

Country Status (7)

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US (1) US5037962A (fr)
EP (1) EP0363730B1 (fr)
JP (1) JPH02142857A (fr)
KR (1) KR900006451A (fr)
BR (1) BR8905111A (fr)
DE (2) DE3834530A1 (fr)
ES (1) ES2057041T3 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW233304B (fr) * 1992-04-02 1994-11-01 Hoechst Mitsubishi Kasei

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2007382A (en) * 1932-08-16 1935-07-09 Celanese Corp Production of dispersions
DE2833854C2 (de) * 1978-08-02 1980-09-04 Hoechst Ag, 6000 Frankfurt Neue marineblaue Dispersionsfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung zum Färben oder Bedrucken von synthetischen Fasermaterialien
DE2921210A1 (de) * 1979-05-25 1980-12-04 Hoechst Ag Faerbestabiler monoazofarbstoff, dessen herstellung und verwendung
DE2948016A1 (de) * 1979-11-29 1981-06-11 Basf Ag, 6700 Ludwigshafen Faerbestabile modifikation eines dispersionsfarbstoffes
DE2950588A1 (de) * 1979-12-15 1981-06-19 Hoechst Ag, 6230 Frankfurt Faerbestabiler monoazofarbstoff, dessen herstellung und verwendung
JPS5742982A (en) * 1980-08-25 1982-03-10 Nippon Kayaku Kk Dyeing and printing of hydrophobic fiber
DE3121320A1 (de) * 1981-05-29 1982-12-16 Hoechst Ag, 6000 Frankfurt Neue faerbepraeparationen, verfahren zu deren herstellung und deren verwendung zum faerben und bedrucken von synthetischen fasermaterialien
DE3125159A1 (de) * 1981-06-26 1983-01-13 Cassella Ag, 6000 Frankfurt Faerbestabile modifikation eines dispersionsfarbstoffs, verfahren zu ihrer herstellung und verwendung
DE3242309A1 (de) * 1982-11-16 1984-05-17 Hoechst Ag, 6230 Frankfurt "faerbestabiler monoazofarbstoff, verfahren zu seiner herstellung und dessen verwendung"
DE3342691A1 (de) * 1983-08-31 1985-03-14 Bayer Ag, 5090 Leverkusen Mischungen von dispersionsfarbstoffen
DE3533980A1 (de) * 1985-09-24 1987-03-26 Cassella Ag Monoazofarbstoffe, ihre herstellung und verwendung
IN169343B (fr) * 1986-04-05 1991-09-28 Cassella Farbwerke Mainkur Ag

Also Published As

Publication number Publication date
EP0363730A3 (fr) 1991-10-02
DE58908272D1 (de) 1994-10-06
BR8905111A (pt) 1990-05-15
JPH02142857A (ja) 1990-05-31
DE3834530A1 (de) 1990-04-12
ES2057041T3 (es) 1994-10-16
KR900006451A (ko) 1990-05-08
US5037962A (en) 1991-08-06
EP0363730A2 (fr) 1990-04-18

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